Orgoreview

Give the structure of an unknown compound A (C₅H₈O) that is chiral ((R)-enantiomer), shows a strong absorption in the infrared spectrum at 3200-3550cm^-1 and undergoes catalytic hydrogenation (H₂/Pd) to give a new compound (C₅H₁₀O) that is achiral (not chiral) and shows a strong absorption in the infrared spectrum at 3200-3550cm^-1.